Episode Transcript
Jess Schultz: [00:00:00] I just kind of trust the process. That's how I've always operated in sales. Meaning like for me it's like, okay, I'm gonna, I run a weekly newsletter where I do kind of my nurture marketing and my thought leadership. I. I post on LinkedIn two to three days a week. I try to do one podcast a quarter, like I have kind of like my little quotas that I've self-imposed, and I know that as long as I do those things for me consistently, every week, every month, every quarter, I always have enough pipeline.
And statistically, I know that if I'm doing all those things consistently. I'm always gonna have 10 conversations in close too, so like it's always gonna work out.
Tracy Young: Hi. Welcome to Path to Growth. I'm Tracy Young, co-founder and CEO of Tiger Eye. Today we are joined by Jess Jolt, founder at Amplify Group.
Jessica, welcome.
Jess Schultz: Thank you. Thanks for having me. [00:01:00]
Tracy Young: So to start, tell me about growing up. Tell us about mom and dad, what you learned from them.
Jess Schultz: I grew up in Florida and both my parents are entrepreneurs. My mom's been an entrepreneur since she was 25. So the fact that she started a business that young, and then to think about it being 40 years ago, I grew up with a lot of good role models.
Tracy Young: Yeah. So she must have so supportive of you moving from, I think it's venture capital for Founding Amplify Group.
Jess Schultz: Yep.
Tracy Young: Correct. And she was excited about it.
Jess Schultz: Yeah, I think we both always knew that I would go out of my own someday. It was just kind of a matter of when and what that would look like. So she's been very supportive.
Tracy Young: So how did you get into sales? Walk us through that journey. You could have done anything. I.
Jess Schultz: Yeah, I guess like many people, I don't think they give a lot of great career counseling. I don't know if that's changed in college. So it's like I majored in finance because my parents were CPAs, so it seemed, you know, and I was good at math [00:02:00] and I went to work at a bank after college just 'cause it felt like that's what you're supposed to do with a finance degree.
I don't really say like, I knew. All my options available to me. I just kind of figured it out as I went. But when I went into banking, I was originally in operations and I was working with the sales team quite a bit, and I just was always really attracted to sales from like very early on. And so I knew pretty quickly that that's where I wanted to end up.
I love working with clients. I love working with people. I love kind of like the psychology of sales, but I think also think like that operations foundation of my career makes me a good seller because so much of sales is. You know, good project management and running a good process. So yeah, so eventually I got into sales, but that was kinda the path.
Tracy Young: Mm-hmm. Tell us about Amplify. What inspired you to found the company and how did you identify the need for fractional go to market and Rev ops leadership in the market? I.
Jess Schultz: Yeah, so I was in a sales role at a company called TriNet, and I was in charge of our VCPE channel [00:03:00] sales. My role was to build relationships with investors and ultimately to sell our product into the portfolio.
And so I built a ton of relationships in the three years that I was there with investors. And eventually one of them ended up recruiting me to join the fund. So during my time there, which I didn't really have aspirations to work in venture capital per se, it just kind of happened. But I'm really grateful for that experience.
But it was during my time there when I was working with our founders who were all seed and series A. And because I came from, as I say, like a classically trained sales background, I had worked in sales and marketing roles at really large public companies. And so I felt like I'd witnessed what kind of best in class looks like.
But then I newly understood what it was like to be a startup and like wearing five hats at the same time, working on with a really small budget, with a really lean team. And so I was able to kind of take those two experiences and guide our founders in many ways on like. What best in class looks like, but what was actually achievable with their size team and their size [00:04:00] budget.
And I just found really quickly that that was the part of investing that I enjoyed the most was like working with our founders one-on-one. And as much as I loved the experience investing, I just think I'm more of an operator. I really enjoyed being in the company and more like ingrained in the day to day.
So it was the time at the VC that made me realize that this was a real need in the market. And then also that I think I had a. A unique background and perspective to help solve the problems. So after a year at the VC, I started Amplify. So I've been in business now for three years and counting. So, so far
Tracy Young: so good.
Congratulations. I mean, it sounds a lot like you're still doing that job that you were with helping founders and helping them, you know, think about their business in a more strategic way, but you're not limited to just the portfolios within. That venture fund, you can actually help anyone comes to you.
And so what advice would you give founders? Like when, when should [00:05:00] they be thinking about bringing on a fractional CRO or a head of rev ops?
Jess Schultz: My sweet spot personally is when they found. Early signs of product market fit. So there's some revenue, there's there, there. And the founder, as I'm sure you know, because I saw that you, this is not your first rodeo founding a company either.
Product market fit is squishy and I think no one ever fully knows if they have it. There's just like certain signs, but I think. Again, generally like broad strokes, roughly amount around a million a RR. When you have 20 or 30 customers, like you start to feel like there's a, there, there, that's when I think it's time for the founder to stop being the sole producer and, and running in a founder led sales fashion and really hand the baton off and elevate themselves to being CEO and kind of chief strategy officer.
So that's when I like to come in. 'cause particularly with the companies I worked in, our portfolio with, many of them, they reached that inflection point, but then they went to just go hire [00:06:00] either a VP of sales or an account executive right off the bat, but they didn't really do anything to prepare for that hire.
They just kind of hired them and they thought, oh, I'll just hire a sales person and the person will come in and everything will be fine. And I think you probably know as well as I do, like that's not how it works. There's some preparation that has to go in to making sure we have things documented and, and we have the right systems in place and we've thought through the compensation plan and we have the right incentives in place.
And so there's a lot of preparation I think that should go into preparing for those hires before you just make them. And so that's when I like to come in, is like, okay, there's some signs of product market fit. We know we need to scale beyond founder led sales. How do I do that in the most efficient way and set that those reps up for success so that that transition doesn't like result in any stalling of our growth or reduction in our conversion rates when that happens.
Mm-hmm.
Tracy Young: Mm-hmm. And how do you best embed yourself into these organizations to drive impact? Like how often, what's a cadence of meetings [00:07:00] that you're actually physically there or remotely there with the team?
Jess Schultz: Yeah, great question. I start all of my engagements off with a go to market audit. So it's like a formal process that I've developed where I really audit like every aspect of their go to market.
So everything from their website, competitive analysis, ICP, and buyer personas, you know, like their sales processes, their systems. So like that audit helps me get really like a strong understanding of current state and then also futures. Where we need to be future state. 'cause part of that will be me understanding where they're at with revenue, fundraising, runway, all of that.
Like trying to take that into account as we build a plan. And so then that's a roughly 30 day process. So that's where we align on like these are the things we're gonna look to accomplish. And then after the audits complete, we move into execution mode. I would say that for most clients I have, I join their weekly sales meeting where we go through pipeline, and that's just more like tactical blocking, blocking and tackling of like what deals are in the pipe, [00:08:00] strategizing, like how to get those closed, et cetera.
And then there's usually a separate weekly or biweekly call where we're talking about more like initiatives. So like marketing campaigns that we wanna test or PR initiatives that we're working on, or process improvements that we wanna make. So I really keep those things separate, like, you know, the blocking and tackling and the more strategic side of initiatives.
And then I'm on Slack with. Clients all day, every day. So I think most of them tell me like, I really do feel like just a member of their team. So we have kind of like those dedicated synchronous times, but just a ton of asynchronous communication outside of that as well.
Tracy Young: And then at what point do you help them hire a full-time CRO and replace yourself out of the engagement?
Jess Schultz: It just really depends for every client, but I do say I aim to be a bridge, not a barnacle like that. I'm always a temporary solution, not a full-time forever. I would say most clients end up working with me nine to 12 months. It's been a little [00:09:00] bit longer the last year, but I think that's just a reflection of like the fundraising and environment in the economy.
Meaning they're delaying hiring that full-time person because it's a little bit more expensive and it's an unknown. Whereas like I'm a known variable and I think people are just trying to mitigate change in this environment. But yeah, in a normal, good economy, I think it's like a six to nine month process, and usually around month six is when I would like to bring someone in.
It's not always a CRO because they might not need. A revenue leader, yet I'll be teaching the, the CEO, how to be that leadership. But we definitely wanna bring in like an account executive usually by month six, so that then I get three months of crossover with that person to really get them ramped trained and make sure that's a smooth transition.
Tracy Young: That makes a lot of sense to me. I mean, having, having failed on this hire many times, it's just so costly to hire the wrong person. Yes. And it sounds like you have a playbook that you know are common, common best [00:10:00] practices that just make sense for any first sales hires. In your experience, what are the most common go to market in rub ops mistakes that founders make early on?
What are the patterns you've seen?
Jess Schultz: Almost always there's a lack of clarity on ICP and buyer persona, and then as a result of position and like. Subsequently positioning. For example, like I'll come into a lot of companies and they're, I'm like, who's your ICP? And they're like, oh, HR leaders within Enterprise.
And I'm like, that's too broad. Like, or a million dollar in revenue company. Like, we can't be that broad. We need to get way, way more specific. So it's a process of really helping. And I, I tell clients, like most of the time, especially founders, right? They know the answers. So I say, I'm like the chief question asker.
Really, it's like I know how to ask them the right questions and press them to think about things critically in the right way so that we get to the answer, but they have the answer. And it's a matter of [00:11:00] like those conversations where I ask the right questions, coupled with me analyzing their existing customer base.
Like looking at like not just what they've told me their ICP is, but like who are their customers today? What are the commonalities in that? Then getting more specific. Than just, again, like HR leaders, like with one company, we realized like it wasn't just out of benefits that we were selling to. We realized that if that head of benefits had been in their role for three years.
We think that was probably 'cause they had the most political capital or enough political capital at that point to get the sale done. But like three years seemed to be our sweet spot of when we would, we would really close deals. And also if that person had an MBA and a consulting background, we noticed that that really was helpful in us closing deals.
So it allowed us to get so much more specific at like targeting and, and who we were selling to when we had those extra data points. Not just the title alone. So it's like really narrowing in on that and getting specific is definitely one, I [00:12:00] guess again, just like missed opportunity. But when we get that right, we see a lot more success.
The other thing would be just basic data hygiene. Like that's a huge problem for so many startups. You know, there's just bad raw data in the system. There's bad pipeline data, and so it's really hard. Like one of the first things I try to get to is just like a baseline metric. 'cause I'm like, it's hard for us to say if we're improving or not.
We don't even know what. The baseline is, and so kind of establishing that and then from that point forward we can start to track like, are our deal cycles getting shorter? Are conversion rates getting better? Is our ICP actually who we're closing? Or like, what about our closed one or flows Lost Analysis is telling us different information.
So kind of building the right data, hygiene and processes and habits is another big one. And then I would say the third one is just consistency. Like, because these are lean teams and sometimes they don't [00:13:00] know exactly what they should be doing, so they try something, then they try something else, and it's all these like little sprints and it's not really consistent.
Effort. And so I think what I bring to engagements is that accountability buddy and getting them to, to be consistent, truly for three to six months on a given strategy or tactic. And like that's when we really see things start to click.
Tracy Young: Mm-hmm. You talk about measurements and baseline being important and being able to, you know, test from there and measure.
How has the role of Rev Ops evolved and what trends are you seeing for the future of revenue operations?
Jess Schultz: Yeah, I think it was, I don't know about anymore, but beginning of last year it was like the number one title, like of open jobs on LinkedIn or something, sorry, mean. It's definitely a growing need and a recognized need for companies of all sizes.
I think the biggest thing we've seen, like as an evolution, as I'm sure you know since you're in the [00:14:00] space as well with Tiger Eye, is this concerted effort to look at operations across the entire go-to market team and not just these silos that we used to see of sales ops and marketing ops and CS ops all operating independently.
So this like. Holistic view of it and the realization that all of those things are so interdependent and interconnected. So I think that's a great thing. And obviously there's just a lot more tooling available at a more reasonable price point than there ever was. You know, simple things like data enrichment, right?
Like we only used to have ZoomInfo available to us at a thousand dollars a month, and that was out of price range for a lot of startups. And now you can get Apollo for 50 bucks. You know, like the fact that some of the price point. On those things has come down is really allowing people to adopt best practices and be smarter and better with rev ops as well.
So yeah, I'm excited about those trends.
Tracy Young: It's gonna make all companies a little bit smarter, a little bit more [00:15:00] strategic and better. Yep. What are the keys to building a successful go to market strategy today? The world's changed, right? Yeah. Information differently. So what? How is it different today, I guess?
Jess Schultz: Some things I think are the same in that like the fundamentals are still really important, right? Like getting, getting super clear on who your ICP is. Your buyer persona, your positioning, like how are you truly differentiated and different, and like having that be cohesive and clear and consistent like that is still really, really important.
That and brand. I would say that hasn't changed and I don't think it will. So I try to counsel companies. I'm like, I know we have all these shiny new objects with ai, but those fundamentals are still the base, the baseline of any AI even helping you. Like if we don't have those things right, it's hard for, for AI to be even helpful.
So I still think the fundamentals matter a lot. I think. What AI has done too though, [00:16:00] is that it's made it a lot more noisy, right? It's so much easier for PE and the price points coming down has had a negative effect in the, from the perspective that like everyone and their mother can for $50 a month stand up an automated outbound sequence, and so we're all inundated.
With so much cold outbound, it's easier to get blogs and and content written. So there's so much content. It's like kind of overwhelming and noisy. So I think it's, it's nice that AI has made some of those things easier, but I think it also then muddies a lot of messages because it's so noisy. So I think the brands that are gonna win are those that kind of figure out how to leverage ai.
But. Still remain very human like. I think the brands that are winning are the ones where the senior executive team is investing a lot in thought leadership and their human side of the brand, like telling their story through podcasts, through LinkedIn, like [00:17:00] really? Having like the person behind the brand's voice be very evident.
I mean, we're seeing that with sales reps too, right? Where actual sales reps are like mini influencers within companies on LinkedIn and stuff. So I think that's gonna be a trend that prevails. 'cause again, it's like that human connection. At the end of the day, sales is always gonna be a human. There's always gonna be a human element to it.
So yeah, I think that's maybe how it's changing is like this whole mini influencer thought leadership thing is being more important. And then I think just leveraging ai, where to go into discovery calls smarter, right? More prepared. Like the fact that you can feed it a 10 k and you know, get every insight about that without spending hours and hours is incredible.
So like, I think the sales reps that are leveraging it to just be smarter and more prepared are also gonna win.
Tracy Young: And it so resonates with me with all this AI content. It's like a conveyor belt of just like crap as being fed into my inbox and messages every single day, and it's only gonna [00:18:00] get worse.
Yeah. And the ones that stand out, as you mentioned, there's a human side to it. You can just, you can just tell this was not written by ai. This was written by someone who actually. Is, you know, thought about me.
Jess Schultz: Yep. I actually never use AI for cold outbound. I, and I coach my clients not to either. I'm like, it's already cold.
We don't need to make it less human like it needs to be like, you can automate it, but write the message as a human being. That's my opinion.
Tracy Young: How do you see the B2B sales process evolving? Or do you, maybe it won't. 'cause you always talk about fundamentals and you know, things. There are things that just don't change when it comes to selling to humans.
Requires a human on the other end.
Jess Schultz: Yeah, I, but I think a completely, I agree, the fundamentals don't change, but again, I just think AI lets us be hopefully faster, right? Like I have, I'm a fan of fireflies, but there's a ton of tools out there now that do like conversation intelligence, right? But like, it's incredible that I have that join every [00:19:00] call with me.
It feeds the entire thing into my CRM. The call notes are there, it captures action items. It actually does it. Correctly. You know, like I'll hang up and I'm like, oh yeah, those were all the action items. So it's like there's so much time savings that's happening now with little things like that. So I think like hopefully people are leveraging those like easy wins that again, are not removing any of the human element of the process at all.
They're just eliminating a lot of the administrative aspects of the job. And I love being able to go back to those conversations too before you go into a pricing or proposal conversation and re-listen to those calls. Like that's super helpful. Because there's little things that you just forget or or missed in the first pass of the conversation.
So I do think AI is going to be instrumental in helping the best sellers that take a human approach be 20% better than they were or, or maybe it's even more than 20%.
Tracy Young: Switching gears a bit, the sales industry looks the way it does, and it doesn't [00:20:00] look particularly like near you. Yet, here we are. Yeah. What do people get wrong about sales and, and specifically mostly because I've met so many women who just don't think it's an option for them, that salespeople look a certain way and, and yet, you know, anyone could be great at sales.
So what do you think people get wrong about sales?
Jess Schultz: Yeah, I mean, you've probably read the stats. I don't remember the exact numbers anymore, but actually. Statistically women are better sellers, meaning like there's actually higher close ratios and higher quota attainment on average for women versus men.
And that's not like, again, to say women are better than men or whatever. It's just that we tend to approach things a little. Like, and I'm being general, not everyone is the same, but in general, women tend to be a little bit more empathetic, better listeners take a more human approach. And so I think that does resonate with a lot of buyers.
But I think maybe what people are getting wrong is when they're just not [00:21:00] human and they have like. Box thinking, and they like very linear thinking and they can't think outside the box. For example, like I had one client come to me and he's like, it was a large enterprise sale. And he's like, well, we think we've got the deal closed, but you know, they're having trouble figuring out whose budget it's gonna come out of, you know, at the prospect.
Like, is it gonna come outta compliance or ops or whatever? And I was like, well, why not? You offer to help them figure out a budget allocation and recommend that the departments share the cost. Like, why does it have to come out of one budget? Why can't we just come up with like a blended, like compliance assumes 30%, ops assumes 30%, and.
Why don't we offer two? Like if that's gonna be easier for them to send them separate invoices, do you care? Because I'm like, I don't know, like it seems like a relatively small thing to send them three invoices for an annual contract. Like that's not like a crazy operational lift. And he's like, oh, you're right.
So I think like people that just can't kind of like problem [00:22:00] solve, it's like, oh, well this is happening, so it's blocked. And it's like, no. Think of creative ways that you can. Address that to make it more buyer friendly, more buyer-centric, there's almost always a solution, so. Mm-hmm.
Tracy Young: And whether it's in sales or marketing or engineering, it's, we're always trying to just figure out how to remove fiction here.
Yes. And especially when it comes to the deal, you wanna land the deal, be creative about it. So those really good coaching you gave them, walk me through what a great day in sales looks like and what a bad day in sales looks like.
Jess Schultz: I think you know this, I'm sure I, I don't get that bothered by the nose 'cause it's like we know they're gonna happen.
So I think for me it's about just having the right habits every single day. And I know those end up leading to the results that I need. So like, I just kind of trust the process. That's how I've always operated in sales, meaning like. And I always come up with my own little formula, and this will be different for every person, but like [00:23:00] for me, it's like, okay, I'm gonna, I run a weekly newsletter where I do kind of my nurture marketing and my thought leadership.
I post on LinkedIn two to three days a week. I try to do one podcast a quarter. Like I have kind of like my little quotas that I've self-imposed, and I know that as long as I do those things for me consistently, every week, every month, every quarter, I always have enough pipeline. And, and statistically, I know that I'm gonna have 10 conversations in close too.
But again, if I'm doing all those things consistently, I'm always gonna have 10 conversations in close too. So like, it's always gonna work out. So I think like more people just hope, I don't know, my, my counseling would be like, figure out what that self-imposed like activities need to be and just be consistent and the rest will work itself out.
And you're gonna have nos and you're gonna have yeses. But like, if you're consistent. Statistically you'll be fine.
Tracy Young: Yeah. Our sales leader calls it the path to plan, like, what are you trying to do this year? Yeah. Start breaking it down [00:24:00] by month, by week, by day, by hour, and go do those things and it'll be okay.
Correct. Yep. I, what do you think? Can you talk about the tension between sales and marketing and customer success teams and like the best way to align them and make them work effectively together?
Jess Schultz: I think so much of that comes down to education, and what I mean by that is like. I think I have like empathy personally, because I started my career in ops.
I moved into onboarding, then I moved into sales, then I moved into marketing. So each time I moved up, I had been downstream, if that makes sense. I. So like when I moved into sales, I've been the onboarding person who received a shitty handover from sales with no information or sales over promising. And then I had to be the bad guy of like, no, we can't do that.
So I, I think like inherently I've had empathy and understanding of what each role does because I've been in them. A lot of times that's [00:25:00] not the case. Like salespeople maybe have never been onboarding people or they've never been marketers. Marketers have never been salespeople, so they don't really truly understand what the, what a day in the life is like for the other one, like I know for me for many years before I really understood marketing, I was like, what do they even do pretty pictures in the website?
Like, I don't what, what, what is marketing doing every day? Like, it just, it didn't make any sense. And I think had they just done a better job. Or more organizations, I would encourage them to do a better job of like, here's what marketing's doing every day. You know, we're not just generating new leads, but we're nurturing the leads that you talk to and like, here's why the information on your deal matters is 'cause then we can help follow up in an intentional way.
I think the more you educate the different functional groups about what the other one's doing and how it's helping. Each other because all of them are helping each other. The more like empathy and understanding there is, and the more people are like, not just, oh, I have to mark this [00:26:00] field on this deal that's annoying.
It's like, no. Now they understand why they're marking that field and how that's gonna help them. So like that's a big thing for me. It's just like education.
Tracy Young: Yeah. And putting, putting each other in, in each other's shoes so they, you know, understand what their priorities are. And essentially all these teams have the same priority, which is revenue for the company.
Jess Schultz: Yeah, exactly.
Tracy Young: Tell us about one person who's helped you become the leader that you are today. I.
Jess Schultz: Yeah, I love that question and I'm like, oh, so many people. But if I had to pick one, I would say Rashad. He was like my first, like it was my first sales role where I was doing like true outbound or true hunting, and he took a bit of a risk on me, you know?
'cause I'd always been in more like account management revenue roles before that. Where I was like upselling or retaining and yeah. Anyway, he took a risk on me. He taught me a lot of what I know and he was a creative problem solver, like I just described, like on deals. So I think like he just kind of showed me by example, like how to think [00:27:00] creatively on deals, like how to, you know.
Multi-thread on deals. Worked with different personalities and he was a really good sales leader. We had so many different personalities on our team, like each rep, and it was always incredible for me to watch him, like we all had deep respect and admiration and worked with him well, yet we were all so vastly different.
I think that's like a superpower for some people.
Tracy Young: That's amazing. I'm really glad you had that model for you early on in your career. It's so funny with sales. I feel like I got better at pitching when I sat with our reps and just heard them pitch and heard them. An objection handle. And I think it's the same thing thing with leadership as well.
Just seeing people in action and being that model. Yeah. And representation for you, Jess, it's been so fun talking to you. What's your parting advice for our listeners?
Jess Schultz: I mean, something I say all the time is like, clarity is how you begin. Consistency is how you win. [00:28:00] So like whatever. If you're not starting something, it's probably just 'cause you need to get clarity on how to start, but then know that you're not gonna have all the answers and you're just gonna have to start and just do it scared, and then be consistent.
Like, hold yourself accountable and stick to it. Like that's how, that's how you win. I.
Tracy Young: Thank you so much for sharing your advice with us today,
